Benzenamine, 3-bromo-4-methyl- → N-(3-bromo-4-methyl-phenyl)4-(4-methyl-piperazin-1-ylmethyl)-benzamide

HRID 1987489Notes

Reaction equation

HRID 1987489 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH2:5].C[O:11][C:12](=O)[C:13]1[CH:18]=[CH:17][C:16]([CH2:19][N:20]2[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]2)=[CH:15][CH:14]=1>>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][C:12](=[O:11])[C:13]2[CH:14]=[CH:15][C:16]([CH2:19][N:20]3[CH2:21][CH2:22][N:23]([CH3:26])[CH2:24][CH2:25]3)=[CH:17][CH:18]=2)[CH:6]=[CH:7][C:8]=1[CH3:9]

Participants

3

Reactant 2

HCID 82187Benzenamine, 3-bromo-4-methyl-HCID 782222Methyl 4-((4-methylpiperazin-1-yl)methyl)benzoate

Product 1

HCID 10309714N-(3-bromo-4-methyl-phenyl)4-(4-methyl-piperazin-1-ylmethyl)-benzamide

Procedure

Another process, depicted in Scheme 2, involves reacting 3-bromo-4-methyl-aniline with 4-(4-methyl-piperazin-1-ylmethyl)-benzoic acid methyl ester to obtain N-(3-bromo-4-methyl-phenyl)-4-(4-methyl-piperazin-1-ylmethyl)-benzamide. The latter is reacted with 4-(3-pyridyl)-2-pyrimidine amine (which is obtained by reacting cyanamide with 3-dimethylamino-1-pyridin-3-yl-propenone) to obtain imatinib.

Sources & evidence

ORD record
ord-f60f8ac9bc7f4f63bb0978390afe8a46
Source dataset
uspto-grants-2009_06
Patent number
US07550591B2

Reaction notes

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